Question 2: Use arrow-pushing to propose the mechanism for each of the following transformations. Indicate the nucleophile and electrophile in each step. H-Br: H-CI:

Part A Draw the product formed when the structure shown below undergoes substitution with OH™. Interactive 3D display mode Br H CH3 Draw the molecule on the canvas by choosing buttons from the Tools (for bonds), Atoms, and Advanced Template toolbars. The single bond is active by default. Show the appropriate stereochemistry by choosing the dashed or wedged buttons and then clicking a bond on the canvas.

ivatives: Nucleophilic Acyl Substitution Reactions - EOC [References] From the table of available reagents select the one(s) you would use to convert butanoic acid to each of the following products: (Use the minimum number of steps; from one to six are required. List reagents by letter in the order that they are used; example: fa. NOTE: Assume that a normal aqueous (or mild acid) workup follows each reaction; you do not need to add reagents for the workup.) Reagents Available a. benzene/AlCl3 d. H2O, H2SO4 g. LiAlH4 j. PBг3 b. (CH3)2CuLi e. H₂, Pd/C h. NaCN C. CH3NH2 f. K* -OC(CH3)3 i. NH3 k. Dess-Martin periodinane I. SOCI₂ 1-butanol butanenitrile

Section A: Apply your knowledge 1. Decide whether the following nucleophiles would react with a ketone, aldehyde, or both and draw the corresponding product(s). If a reaction seems unfavorable explain why/how a product can still be obtained. H₂O Or MeOH Or O HO OH Or H2N—Ph Or H3C CH3 Or 1.1 HO HN—CH3 Or